193146-85-9

Basic information

• Product Name: Galantamine Hydrobromide Racemic (15 mg)
• Synonyms: Galantamine Hydrobromide Racemic (15 mg);rac GalanthaMine HydrobroMide;Galantamine hydrobromide racemic
• CAS NO: 193146-85-9
• Molecular Formula: C17H22BrNO3
• Molecular Weight: 368.26548
• Mol File: 193146-85-9.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Galantamine Hydrobromide Racemic (15 mg)(CAS DataBase Reference)
• NIST Chemistry Reference: Galantamine Hydrobromide Racemic (15 mg)(193146-85-9)
• EPA Substance Registry System: Galantamine Hydrobromide Racemic (15 mg)(193146-85-9)

Safety Data

• Hazard Codes: T,Xi
• Statements: 25-38-43
• Safety Statements: 26-45
• RIDADR: UN 2811 6.1 / PGIII
• Hazardous Substances Data: 193146-85-9(Hazardous Substances Data)

Upstream product

• 510-77-0 (-)-narwedine 
• 26601-10-5 (-)4a,5,9,10,11,12-hexhydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-one 
• 934415-11-9 galantamine 
• 807362-55-6 (-)-galantamine tartarate 
• 357-70-0 Galantamine 
• 357-70-0 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef ][2]benzazepin-6-ol 
• 510-77-0 (4aS,8aS)-rel-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-one 
• 122584-18-3 N-(4-hydroxyphenethyl)-N-(2-bromo-5-hydroxy-4-methoxybenzyl)formamide 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 2973-59-3 2-bromoisovanillin 
• 179107-93-8 N-(p-hydroxyphenylethyl)-N-(6-bromo-3-hydroxy-4-methoxybenzyl)amine 
• 7318-55-0 (4aR,8aR)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-one 

Downstream Products

• 146274-40-0 (-)-(4aα,6β)-6-chloro-4a-5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-e,f][2]benzazepin 
• 60755-80-8 O-Demethylgalantamine 
• 41303-74-6 N-desmethyl galantamine 

Relevant articles and documents

A Nivalin industrial preparation method (by machine translation)

The invention relates to a technical field of drug synthesis, in particular relates to a preparation method of the galanthamine hydrobromide. Preparation method of this invention comprises the following steps: (1) the racemate narwedine as raw materials, adding resolution solvent to get levorotation narwedine; (2) L narwedine [...] butyl boron lithium hydride reduction shall be galantamine free alkali, further and hydrobromic acid shall be galanthamine hydrobromide. (by machine translation)

Stereoselective syntheses of galanthamine and its stereoisomers by complementary Luche and L-selectride reductions

A diastereodivergent approach for the stereoselective syntheses of all four stereoisomers of galanthamine, (-)-galanthamine 1, (+)-galanthamine 2, (-)-epigalanthamine 3, and (+)-epigalanthamine 4, from (±)-narwedine 5 is reported. Thus (±)-narwedine 5 was resolved by dynamic kinetic resolution to obtain enantiomerically pure (-)-narwedine 6 and (+)-narwedine 7. Each enantiomerically pure isomer of narwedine was subjected to Luche and L-selectride reactions to obtain all four isomers of galanthamine. In these reactions, the (-)-galanthamine 1 and (+)-galanthamine 2 isomers were obtained with an enantiomeric purity of >99.5%, whereas (-)-epigalanthamine 3 and (+)-epigalanthamine 4 are obtained with a chiral purity of >97%. The axial hydride attack by the Luche reduction and the equatorial hydride attack by the L-selectride reduction on the cyclic enone system are explored in the stereoselective synthesis of the galanthamine isomers and thus it was demonstrated that the stereoselective synthesis involving the Luche and L-selectride reductions are complementary in yielding enantiomeric stereogenic centers from a prochiral carbonyl group on the cyclic enone system.

An improved process for the preparation of galantamine hydrobromide

The present invention relates to an improved process for the preparation of [4aS,6R,8aS]-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-ol of Formula I